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10 Ways to Lose at Selling Learning Systems: For LMS Vendors

How to Fail at Selling Learning Systems - Advice for LMS vendors from independent software analyst John Leh

LMS vendors, I owe you a post.  It’s hard to believe nearly two years have passed since I last shared tips for selling learning systems.  But since the LMS market is on fire, you’ve probably been too busy to notice.  I hope you’ve been too busy winning.

We’ve certainly had our hands full.  This year, in addition to launching “The Talented Learning Show” podcast, writing 20 in-depth articles, hosting 5 webinars and developing several commissioned industry reports, we’ve been up to our eyeballs in an endless series of comprehensive LMS selection assignments.  In fact, we just completed two concurrent full-scale LMS selection projects — one for a corporate extended enterprise client and another for an international professional association.

In our selection process, the first step involves working with clients to define their requirements accurately.  Then we recommend 4 highly qualified, matching vendors to evaluate in a formal RFP process.  (Learning systems buyers are always more successful when they invest their limited time evaluating qualified vendors for their specific business situation vs. trying to qualify 700 vendors themselves.)


With 8 total finalists, my head is still spinning from analyzing more than a thousand pages of RFP response documents, sitting through 24 hours of demos and critically (sometimes ruthlessly) evaluating a diverse cast of sales characters as they pitched their solutions.

The LMS Sales Process: What Counts?

As you may know, this isn’t my first sales rodeo.  Before founding Talented Learning, I was an LMS sales guy for 13 years and competed in hundreds and hundreds of learning systems sales opportunities.  I won and lost my fair share but was unaware of my level of effectiveness relative to my sales peers.

Sales reps rarely get a chance to see peers in action, so it’s difficult to compare your sales prowess based on anything other than annual sales volume and the tidbits shared by the common solution architects.  Now as a selection consultant, I have a better view than most of the best and worst sales people from all over the world.  It’s a fascinating side benefit of my job.

What do I notice?  The list is deep, wide and critical.  For example:

  • How quickly do sales reps respond to inquiries?
  • How deeply do they understand my client’s business needs?
  • How thorough are their questions?
  • Do they seem fully prepared for demos?   How do they demo?
  • How candid and honest are their answers?
  • Are they on time?
  • Are they leveraging their executives – circling the wagons?
  • Are their clothes pressed, shoe shined and hair combed?  (Yes, I really need to say this unbelievably).
  • What is their level of knowledge about their own solution?

That’s just a small sample from my thousand-point checklist.  I may be a tough critic, but when I see a stellar sales performance, I’m quick to give credit.  On the other hand, when I see a train wreck, I’m equally quick to notice, chuckle and not invite them to compete again for a while.  I rarely share criticism directly with vendors unless I’m asked, or unless I’m in the mood to write.  Lucky for you, today I have plenty of fresh feedback from my recent experiences!

Why Sales Performance Should Be a Priority

Selling learning systems is never easy.  The quickest selection processes take 90 days and require a ton of work.  There can be only one winner and second place is worse than 40th.   With 700+ learning management systems as competition, continuous sales improvement is the hidden-in-open-view key to a learning systems company’s future.  Sometimes, a salesperson can do everything right in the sales process and still lose but that doesn’t happen as often as salespeople like to think or tell their executives.

It also turns out that buyers are picky.  Go figure.   They are going to spend a few hundred thousand dollars and put their professional reputations on the line with their final vendor choice.  The reasons why they buy or don’t buy are often subjective and are much deeper than any feature, function or cost factor.

Top 10 Ways to Lose an LMS Deal

The problem with winning, though, is that it’s time-consuming, both during the sales process and after.  So if your organization is winning too many deals and your calendar is fuller than you’d like, here are some top ways I’ve seen to lighten the load and lose a deal:

1) Rather than customizing your RFP response, just reuse a boilerplate proposal and be sure to avoid specifics about the opportunity at hand.


2) Skip the spellcheeck.

3) Structure your pricing in an overly complicated manner that does not address the specific requirements in the RFP.  Don’t forget to itemize plenty of low-cost options that are actually mandatory, so buyers are forced to untangle these features and debate the merits and cost of each.

4) Avoid research to profile your buyer.  Don’t bother investigating their industry, their business strategy, their positioning, their brand names and other publicly available information.  Ignore LinkedIn information about their organization and leaders.

5) Don’t illustrate a deep understanding of the business need in your RFP or product demonstration.  Instead, assume all purchasing scenarios are essentially the same and you’ve seen these challenges before.

6) In the final demo, ask lots of discovery questions and try to tailor your demo on the fly.

7) Freely use the phrase “you can have anything you want,” or “that will require a slight modification,” but forget to note that your proposal doesn’t include the time or cost to satisfy any of these requirements.

8) If you don’t meet a requirement, purposely misrepresent it.  This is one of my favorites.  It often plays out like this: “Yes, we meet this requirement…”  (And from this point forward, drone on with a convoluted-confusa-answer that describes something else entirely, hoping the buyer isn’t reading or listening closely, or an LMS selection consultant isn’t working on their behalf).

9) Deliver a “spaghetti-on-the-wall” demo where you throw every feature of your system at the buyer and hope something sticks.  You know this is happening when the presenter says, “I don’t know if you need this particular feature or not, but let me tell you all about it just in case,” and then describes it in excruciating detail.    

10) In the final demo, when prospects ask a question that exposes a requirement gap, promise you’ll follow-up with an answer – then conveniently forget to close the loop.


Selling learning systems has always been challenging, but it’s even more so now.  With so many niche players and so many ways to apply learning platforms, you’re likely to face stiff competition from across the spectrum.  It’s impossible to keep ahead of every potential competitor, so selling against competitors is fruitless.  Instead, win the sale by helping buyers see your solution through a lens that focuses on their unique business needs.

The best salespeople perfect their performance the same way elite athletes do.  They systematically optimize their abilities for each of the many elements in the sales process.  You can’t win an LMS deal by excelling in only one step, but if you continually improve each step, eventually you’ll win more than your fair share of customers.

Above all, be ruthless in qualifying opportunities – in or out.  If it’s “out,” don’t stretch.  But if it’s “in,” don’t waste the lead by making junior sales mistakes.  Aim for the win every step of the way.  Chances are you will stand out from the crowd, achieve your goals and become an incredibly busy winner.

Thanks for reading!


Want more insights? Replay our on-demand webinar

Custom Learning Experiences: When No LMS Will Do


Are training revenues the lifeblood of your business? With so much at stake, you can’t afford a learning platform and content that misses the mark. Yet, even with more than 700 LMSs available today, it’s easy to come up short.

So, what should you do when an out-of-the-box LMS can’t meet your commercial training objectives? Join John Leh, CEO and Lead Analyst and Edward Daciuk, Principal Learning Strategist at ExtensionEngine, when they explore this topic in depth. You’ll learn: 

  • Characteristics of a custom learning experience
  • How custom learning experiences can differentiate your training business
  • When this approach does/does not make sense
  • Business drivers for custom experiences vs. standard LMS solutions
  • How to create a multi-year strategy
  • Real-life examples

Replay the webinar NOW!

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John Leh
About John Leh (154 Articles)
John Leh is CEO and Lead Analyst at Talented Learning, LLC. Named among the “Top 20 Global Elearning Movers and Shakers” in 2018 and 2017, John is a fiercely independent LMS selection consultant, blogger and podcaster who helps organizations develop and implement learning technology strategies – primarily for extended enterprise applications. His advice is based on more than 20 years of industry experience, serving as a trusted LMS selection and sales adviser to more than 100 learning organizations with a total technology spend of more than $65 million. You can connect with John on Twitter at @JohnLeh or on LinkedIn.